5-Methylbicyclo[2.2.2]oct-2-ene

Base Information

• Chemical Name: 5-Methylbicyclo[2.2.2]oct-2-ene
• CAS No.: 14803-42-0
• Molecular Formula: C₉H₁₄
• Molecular Weight: 122.21
• DSSTox Substance ID: DTXSID80933286
• Nikkaji Number: J801.425F
• Mol file: 14803-42-0.mol

Synonyms:5-methylbicyclo[2.2.2]oct-2-ene;14803-42-0;Bicyclo(2.2.2)oct-2-ene, 5-methyl-, (1alpha,4alpha,5beta)-;DTXSID80933286;Bicyclo(2.2.2)oct-2-ene, 5-methyl-, (1alpha,4alpha,5alpha)-;5-methylbicyclo[2.2.2]-2-octene;bicyclo[2.2.2]oct-2-ene, 5-methyl-, (1.alpha.,4.alpha.,5.alpha.)-;Bicyclo[2.2.2]oct-2-ene, 5-methyl-, (1.alpha.,4.alpha.,5.beta.)-;14926-88-6

Chemical Property of 5-Methylbicyclo[2.2.2]oct-2-ene

Chemical Property:

• Vapor Pressure: 4.25mmHg at 25°C
• Boiling Point: 153.5°C at 760 mmHg
• Flash Point: 29.7°C
• Density: 0.897g/cm³
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 122.109550447
• Heavy Atom Count: 9
• Complexity: 135

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC2CCC1C=C2

Technology Process of 5-Methylbicyclo[2.2.2]oct-2-ene

There total 23 articles about 5-Methylbicyclo[2.2.2]oct-2-ene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

bicyclo<2.2.2>oct-5-en-2-exo-yl p-toluenesulfonate → 5-exo-methylbicyclo<2.2.2>oct-2-ene (4517-47-9,14803-42-0,14926-88-6)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; for 24h; Heating;

DOI:10.1002/hlca.19840670723

Reference yield:

exo-6-methylbicyclo[2.2.2]octan-2-one tosylhydrazone → 5-exo-methylbicyclo<2.2.2>oct-2-ene (4517-47-9,14803-42-0,14926-88-6) + 3-methyl-tricyclo[3.2.1.02,7]octane + 1-methyl-tricyclo[3.2.1.02,7]octane

Guidance literature:

exo-6-methylbicyclo[2.2.2]octan-2-one tosylhydrazone; With sodium methylate; In methanol; at 20 ℃; for 0.166667h;

at 180 ℃; under 0.05 - 2 Torr; Further stages.;

DOI:10.1021/ja002407+

Reference yield:

bicyclo<2.2.2>oct-5-ene-2-carboxaldehyde (38259-00-6) → endo-5-methylbicyclo<2.2.2>oct-2-ene (4517-47-9,14803-42-0,14926-88-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / hydrazine hydrate; hydrazine sulfate / 65 °C

2: tBuOK / dimethylsulfoxide

With potassium tert-butylate; hydrazine hydrate; hydrazinium sulfate; In dimethyl sulfoxide; 2: Wolf-Kishner reduction;

DOI:10.1021/jo051505g

upstream raw materials:

endo-2-(hydroxymethyl)bicyclo<2.2.2>oct-5-ene

bicyclo<2.2.2>oct-5-ene-2-carboxaldehyde

cyclohexa-1,4-diene

methyl endo-bicyclo<2.2.2>oct-5-ene-2-carboxylate

Downstream raw materials:

2-methyl-bicyclo-[2.2.2]octane